Canmetcon
Record Information
Version1.0
Creation date2010-04-08 22:11:26 UTC
Update date2018-05-29 01:14:11 UTC
Primary IDFDB014715
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameLimonin
DescriptionIsolated from oranges and other citrus fruits (Citrus subspecies). Limonin is a limonoid, and a bitter, white, crystalline substance found in orange and lemon seeds. It is also known as limonoate D-ring-lactone and limonoic acid di-delta-lactone. Chemically, it is a member of the class of compounds known as furanolactones.
CAS Number1180-71-8
Structure
Thumb
Synonyms
SynonymSource
7,16-Dioxo-7,16-dideoxylimondiolHMDB
CitrolimoninHMDB
DictamnolactoneHMDB
Evodia fruitHMDB
Evodia fruit (JP15)HMDB
EvodinHMDB
Evodine?HMDB
Limone?HMDB
Limonoate D-ring-lactoneHMDB
Limonoic acid 3,19:16,17-dilactoneHMDB
Limonoic acid, di-delta-lactoneHMDB
ObaculactoneHMDB
Evodia fruit (TN)biospider
Limonoate d-ring-lactonebiospider
limonoic acid 3,19:16,17-dilactonebiospider
Predicted Properties
PropertyValueSource
Water Solubility0.08 g/LALOGPS
logP3.47ALOGPS
logP2.46ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)17.61ChemAxon
pKa (Strongest Basic)-3.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area104.57 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity114.72 m³·mol⁻¹ChemAxon
Polarizability47.86 ųChemAxon
Number of Rings7ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC26H30O8
IUPAC name19-(furan-3-yl)-9,9,13,20-tetramethyl-4,8,15,18-tetraoxahexacyclo[11.9.0.0²,⁷.0²,¹⁰.0¹⁴,¹⁶.0¹⁴,²⁰]docosane-5,12,17-trione
InChI IdentifierInChI=1S/C26H30O8/c1-22(2)15-9-16(27)24(4)14(25(15)12-31-18(28)10-17(25)33-22)5-7-23(3)19(13-6-8-30-11-13)32-21(29)20-26(23,24)34-20/h6,8,11,14-15,17,19-20H,5,7,9-10,12H2,1-4H3
InChI KeyKBDSLGBFQAGHBE-UHFFFAOYSA-N
Isomeric SMILESCC1(C)OC2CC(=O)OCC22C1CC(=O)C1(C)C2CCC2(C)C(OC(=O)C3OC123)C1=COC=C1
Average Molecular Weight470.5116
Monoisotopic Molecular Weight470.194067936
Classification
Description belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassTriterpenoids
Direct ParentLimonoids
Alternative Parents
Substituents
  • Limonoid skeleton
  • Steroid lactone
  • 11-oxosteroid
  • Oxosteroid
  • 2-oxosteroid
  • Steroid
  • Naphthopyran
  • Naphthalene
  • Delta valerolactone
  • Dioxepane
  • 1,4-dioxepane
  • Delta_valerolactone
  • Pyran
  • Oxane
  • Dicarboxylic acid or derivatives
  • Tetrahydrofuran
  • Heteroaromatic compound
  • Furan
  • Carboxylic acid ester
  • Lactone
  • Ketone
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Oxacycle
  • Dialkyl ether
  • Oxirane
  • Ether
  • Organooxygen compound
  • Organic oxide
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 66.37%; H 6.43%; O 27.20%DFC
Melting PointMp 298°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical Rotation[a]D -125 (Me2CO)DFC
Spectroscopic UV Data285 (e 38) (EtOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-004i-7091800000-d189c180a34aeb636eb4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0fk9-0000900000-a4ab208d1fffee15d3dfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0imr-0012900000-ed371143180c1aea6bc7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000t-9120100000-66524d5b327a652ced01View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00or-0000900000-75a3d9f8a0f1fae14750View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0g2c-1002900000-4048ea92e5c743c331acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0002-4009200000-94a0f7fc00188c6b3e35View in MoNA
ChemSpider ID205258
ChEMBL IDNot Available
KEGG Compound IDC03514
Pubchem Compound ID235284
Pubchem Substance IDNot Available
ChEBI ID16226
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB35921
CRC / DFC (Dictionary of Food Compounds) IDJVF49-D:JVF49-D
EAFUS IDNot Available
Dr. Duke IDLIMONIN
BIGG IDNot Available
KNApSAcK IDC00003719
HET IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDLimonin
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti cataleptic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti feedantDUKE
anti leukemic35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
anti malarial33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
Flavours
FlavorCitations
bitter
  1. Ayana Wiener, Marina Shudler, Anat Levit, Masha Y. Niv. BitterDB: a database of bitter compounds. Nucleic Acids Res 2012, 40(Database issue):D413-419. DOI:10.1093/nar/gkr755
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).